Biggest Mistakes Women Make When Dating


Calling all single ladies! Dating is quite the adventure, right? I’ll say it is!! But dating can be fun, it’s all about perspective AND the approach. You need to enjoy the process and forget the outcome. As women we tend to approach dating a little differently than men – I learned that the hard way! Social Media and Online Dating has created this crazy age of instant gratification where everyone wants it ALL and wants it NOW. This has led to many people making rookie mistakes in dating – including me! What are the biggest mistakes women make when dating? I’m going to share with you about how my journey led me from a really dark place to a place of being HAPPILY SINGLE to finding happily ever after with the RIGHT person. How did I get here? By making A LOT of mistakes along the way!

Biggest Mistakes Women Make When Dating

Who thinks they have the WORST LUCK in love? What if I told you that you don’t? If you keep ending up with the wrong men over and over again then YOU are doing something wrong! Listen, I’ve been there, done that AND wrote a blog about it!! I couldn’t understand what my problem was and why these guys were all out to get me but then I figured it out, it wasn’t them it was ME! There are many people who have bad intentions but most don’t but I was picking the WRONG people and the way I was behaving and reacting to them led me to being disappointed and upset every time. I didn’t make smart decisions and I paid for it. See if any of these biggest dating mistakes sound familiar …

Mistake #1: “Someone should love me for me”

Sure they should BUT when you’re dating you need to put forward the best version of yourself – physically, mentally AND emotionally!! This means taking care of yourself – look good AND feel good, be positive, be someone other people want to be around!! Dress nicely, have good grooming, be healthy – all these will help you attract the right person. People, especially as they get older, don’t want drama! They don’t want negativity and they don’t want a clinger. They want a normal happy life just like you do but we as women tend to bring out the crazy lady from time to time and THAT scares people off! You also need to manage your expectations accordingly in order to have fun dating.

Mistake #2: Letting loneliness and desperation cloud your judgment.

Ever meet someone who you thought was the man of your dreams – you have amazing chemistry with them – you can tell them anything – you are very attracted to each other – then poof he disappears into a black hole of oblivion never to be seen again. Wonder why he ghosted? It’s because you get too comfortable, too fast and jump from 0-60 in 2 dates, maybe he even came along for the ride BUT you left nothing to the imagination and the too much too fast made them lose interest and the greener grass on the other side looked way too appealing.

You don’t have to play hard to get BUT you do need to be HARD TO FORGET! You do this by taking your time, don’t overshare, and take it slow even if they’re rushing. Nothing good can come from rushing a new romance. You miss the red flags and you get caught up in the wrong emotions – I know it feels good with all those love hormones rushing through your body BUT slow and steady ALWAYS wins the race! I’ve been there too, and I was disappointed with the outcome every time. Don’t let loneliness or desperation cloud your judgment in dating.

Mistake #3: Who has ever been caught up in wishful thinking and false hope only to be left with a broken heart?

I know I have, time after time, so have the hundreds of women who have emailed me wondering what happened! Maya Angelou said that “when someone shows you who they are, believe them!” Many of these people don’t ever promise you anything, some even tell you they aren’t looking for anything serious BUT you know differently, right? WRONG! If someone wants to be with you then they will be! You won’t have to stress about it because it’s just going to fall into place where it’s supposed to. Boy did I learn this lesson the hard way! I tried and tried to make things work with some people who were a dead end before it even began but I really believed I could make it work because we had crazy chemistry … boy was I wrong!

Mistake #4: Who is looking for someone to help them carry their baggage?

I can’t tell you enough what a dangerous statement that is! It’s no one’s responsibility to help you carry anything! Deal with your baggage BEFORE finding love! Someone can love you despite your baggage but it’s not theirs to carry. In order to have a healthy relationship, you need to be your own individuals walking forward together on the same path in the same direction. Sometimes you need to lean on each other in difficult times, but expecting them to carry you all the time only leads to bad places. I had to resolve my own issues and baggage post-divorce BEFORE I was ready for a real relationship and I didn’t realize that until I was a couple years into my dating life. I was emotionally unavailable and I was self-sabotaging as a result. When I did deal with it suddenly I found what I was looking for all along.

Mistake #5: You love a good pity party and can’t handle rejection.

When you’ve dated as much as me you get very used to rejection on a grand scale. But after a while, I learned that I needed to decline the invitation to the dating pity partyI realized that rejection was nothing more than a lesson learned. It was then that it clicked, each dating situation put me on a path to finding the real deal because I learned what I did wrong and what they did to me and it led me to being able to recognize the right man when I saw him. So I learned that instead of my pity party I should be grateful for EVERY dating experience good and bad, I learned to be grateful for everything in my life. Daily gratitude does bring love your way, it certainly did for me! I also needed to get over myself … I love the quote by Dita Von Teese “You can be the ripest, juiciest peach in the world, and there’s still going to be somebody who hates peaches.” So there you have it! Remember you reject people too! 

Mistake #6: Who has a laundry list of what they want in a partner?

I sure used to and it was a big one! Just curious, who ditches that list when they meet someone who makes them feel tingly all over? I sure did!! Then I learned that in reality lists don’t work at all. You need to know and stick to your core values and make sure those are compatible. You also need to recognize your main deal breakers. That’s it, that’s all – the rest is just packaging.

Here’s what you should be doing, forget about what they have to offer you and focus on being a great catch yourself. You need to be the person you want to date. Want the hot guy who’s fit and dresses well, well you’ve got to be a hottie who’s fit and dresses well too. The first thing I get my clients to do is write the top 5 reasons someone would want to date them. They can’t be generic like “I have a good sense of humor” they have to be stuff that makes them different and unique, that makes them stand out from the crowd. It’s very competitive out there so you need to be able to market yourself the right way. Show them WHY you’re a prize.

Mistake #7: Are you “one-dimensional”? Have a sense of entitlement?

In order to be competitive in the dating world you can’t be one-dimensional. Be knowledgeable about current events and the world, be a good conversationalist, talk about what you’re passionate about on a date, don’t be generic … it will make you more interesting and confident which is very sexy! Confidence isn’t arrogance however and many women have a sense of entitlement and this is the nail in their dating coffin. Just because you’re smart, successful and accomplished doesn’t make you a “catch”, neither does being attractive. Remember that.

These are just a handful of mistakes women make when dating – they are things each and every women have been guilty of at some point but they are things you can easily fix without changing who you are. You need to be the best version of yourself and this will help you find your happily ever after. Dating can be fun, it really is all about perspective.

READERS: Do any of these resonate with you? What are the biggest dating mistakes you’ve made? Share your thoughts in the comments below!

Your Sister in Dating Bliss,

Single Dating Diva

This is adapted from a talk I gave at the National Women’s Show in Ottawa, Canada.

Copyright Single Dating Diva


  1. I can’t speak for other women but I’ve encounter all of these with men too. Meaning there are so many damaged men on dating sites who refuse to fix themselves and think we should take them no matter what. That bothered me. I will say the rejection one can sting if you are being rejected for a superficial reason then on top of it get responses from men not what I wanted. It was frustrating being turned down by men my age while men old enough to be my father wanted to date me. Made me so depressed.


    • Thanks for you comment Dawn! While this post focuses on women, men also have a lot of things they need to work on. It does hurt to be rejected, no doubt! I’ve been there! But people can’t help who they’re attracted to and just like you’ve rejected people for your own reasons, they have theirs. Being able to deal with rejection is such an important part of dating unfortunately, especially these days! Stay the course, know your values and your deal breakers, with the right perspective you will reach your desired ultimate goal.


    • Yes, Dawn….. All these “mistakes” can be be flipped around and pointed toward men. Oh….. and those older men, your “father’s” age, are probably just sick and tired of women their own ago – I have run into quite a few myself, that are very self centered and silly in there expectations.


      • Not all women that age are like that, but even so, doesn’t mean I want them. An older guy is repulsive to me. Yes repulsive because they overlook my age range (which is 10 years either way)and ignore it. It’s one thing if I meet an older guy and we click and he likes me despite the gap. It’s another if he only likes me because I am older. I run into that one far more. I don’t have daddy issues and don’t want a man my dad’s age.


          • That’s true. I don’t care what people are looking for except when they contact me and my profile stated not for them to do so.


  2. Interesting article! But this leaves long time readers very puzzled!?

    One has to wonder what happened to the Single Dating Diva’s own well publicized “laundry list” for the bad boy alpha males with attitude, as well as with private jets, multi-million dollar business deals, and multiple homes (houses for which she was dreaming of going on furniture & decor shopping sprees)?! As for “one-dimensional” “have a sense of entitlement”, where did her own claims go of being the perfect “alpha female” for these chaps?!

    There’s always the likes of Donald Trump (until his next divorce); Kevin O’Leary; Tiger Woods; etc… to satisfy those set in stone “laundry lists” that so many “one-dimensional” women have…

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    • Thank you so much for being a long time reader and following me on my journey to find love and GOOD NEWS I did find the man of my dreams and we’ve been very happy together for quite some time now!! As you know, because you’re a long time reader, my goal has always been to help others find love, as such I’m trying to help women think a little differently. Yes, I’ve always maintained that I’m looking for someone who’s a strong alpha male because I have a strong personality and through experience I’ve learned that is what works best for me. I did indeed joke about wishing for the millionaire with the fancy cars because I really do love fast cars, but I think you take “tongue in cheek” comments a little too literally. Thank you again for your comment, though, too bad you couldn’t share your real name, I do so love to meet my readers when they’re not hiding behind their computers or pseudonyms! Wishing you a fabulous day and thanks again for sticking around all these years!! Stay tuned for lots more to come!!

      Liked by 1 person

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